Monoazo dye.



UNITED sr-ZI nnrcrrnnnrnonn, on BERLIN, GERMANK-A'SSIGNOB. To Ao'rIEN ensnnnsomrrrflw ANILIN FABRIKATION,

or nnnLm,'cnnMANv.,,

,monoazo DYE.

No Drawing.

To all whom it may] concern:

Be it known that I, Enron Bnn'rHoLn, a subject of the King 'of Prussia, residing at Berlin,G'ermany,' n y post-office address being 61 'Johanniterstrasse, 1, Berlin, S. \V., have invented certain new and useful Improvements in Monoazo Dye and Processes of Making the Same, of which the following is a specification; i

I have found that by diazo'tizingparaaminodiphenylamin and combining the diazo compound-thus formed with resorcinol a new azo coloring matter is obtained which, because of its very remarkable fastness against the action of light is very useful for several-industrial purposes. For example it .may be used in the manufacture of color lakes for lithography, for wall-paper printing and for alcoholic varnishes; furthermore this dyestuif is veryfivell adapted for dyeing woodbrown shades which possess a very good fastness to light. The manufacture of such lakes and the dyeing of wood is performed in the manner usual for such purposes. p

lhc following example serves to illustrate the invention, the parts being by weight: 22 parts of the hydroclilorid of para-aminodiphenylamin are stirred together with 500 parts of water and 36 parts of hydrochloric acid of 1236. specific gravity. After dis: solution the mass is cooled to C. and diazotization performed at this temperature by means of 7 parts of sodium nitrite. vAreson. cinol solution is prepared by dissolving 11. .parts of resorcinol and 23 parts of caustic soda lye of a specific gravity of40- Baum, in about 300 parts of water'a'ndll parts of anhydrous sodium carbonate is'added. 'This, solution is cooled with ice and thediazo compound ispoured into the same and the whole mass stirred continuously. After -."stirring for several hours the formation of the d'yestufi' is complete, whereupon the product of the reaction is saltedout by adding common salt and filtered obtaining thus the sodium compound of the .dyewhich by adding a mineral acid and a hydrochloric acid is converted into the free, dyestufl, which is filtered, washed with water, pressed and dried. The new dye is thus obtained when pulverized in the shape of a greenish black powder which is insoluble in cold Water and with diiliculty soluble in boiling water. This aqueous solution possesses an ,trated liquor animoniae orsom concentratci -trated liquor'annnonize or of conc entrated' f Specificatio'n of'itetters Patent.' lPatefitedcFeb; Z, 1911, Application filed July 18, 1910. Serial No. 572,634.

orange coloration .which colorationis not altered by'adding some conoentrated'liquor' ammonia: orsomeconcentrated caustic soda lye. The dye is easily soluble inalcohol which solution in a suitable concentration shows a yellow brown coloration which coloration on addition of concentrated liquor ammonia: or

of concentrated caustic soda lye turns to red orange. and on addition of concentrated hy-" drochloric acidlchanges to (ice blue; In concentrated sulfuric acid the co oring'mat ter easily dissolves to a yellow brown solution which on the addition of ice shows a blue and grainy precipitate. By the action of strong reducing agfnts the dyestufi' is split 7 up, para-aniinodip 'enylamin being formed;

besides ammo-resorcinol;

The dye produces on wood-from an alco-. holic solution in asuitable concentration a tint which resembles that of light oak-wood. It is also adapted for the manufacture of alcoholic varnishes which varnishes-show a reddish brown tint, I

The present invention is not limited to the foregoing example and more-especially to the special conditions of reaction.

Having 'now described my invention and the manner in which it may be performed what I claim is,- f I As a new article of manufacture the-newhereinbefore described monoazo dyestufi derived from para-aminodiphenylamin and 'resorcinol, which new dyestufima be obtained by diazotizingpar'a-amin iphenyl anun and combining the diazo compound thus obtained with resorcinol,-,which' new' dye is especially adapted'to dyein Of-wood. and for the manufacture of alco olic var; nishes, this dye representing when pulverized a greenish black powder ,which is in:- soluble in cold water and difiicultly's'olw -'b le in boiling water, which aqueous solution possesses an orange coloration, which coloration is not altered by adding somelconcencaustic-soda-lye, and this new dye being easily soluble in alcohol which solution a suitable concentration shows a yellow brown coloration which coloration on addition-of concen caustic soda-lye turns to red' orange and on addition of concentrated hydrochloric acid changes to'dccp blue, this new dye easily dissolving in sulfuric acid to a yellow brown solution which on the addition of ice shows a blue and ggginy precipitate, and this new my hand in presence of tw'o sub scribing W513- dyeilby-thfe actmn ofistrong rgduclillfg aagentzi messes.

suc as or instance stannous c ori an hydrochloric 'acid, being split up whereby ERICK BERTHOLD para-aminodiphenylarnin is formed besides Witnesses:

amino-resorcinol. Hnimy HASPER,

Intestnnony whereof I have hereunto set A WoLnnMAR HAUPT. 

